Sissies Stories

1,006 results
Orientation
Length
Source
Infinite Scroll

Adult Arcade Sissy

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

Dwayne started hanging out with us when I was 18. He was older than us - 28 - but he came across as someone our age. Because he was older a lot of us guys sort of hero- worshipped him - me included. So naturally I was flattered when he began to spend a lot of attention on me in particular. The guys I hung out with were a little wary of Dwayne, because he w...

A Sissy's New Daddy

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

Walking in the door the Friday after my eighteenth birthday, everything seemed great. My parents had gone out of town for the weekend and I was for the first time a truly free man. My older brother had decided not to come home for Labor Day holiday which I was kind of bummed about, we didn't get alone all that well but I still looked up to him. He was one of...

You Can Always Say No Ch. 02

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We had had 'The Talk' in the afterglow of that first evening of sex in our newly-revised relationship, less than a month before we exchanged vows. There is nothing more abjectly terrifying – for either person – than laying bare your soul at such an intimate level. He admitted his wants, needs, and desires; I reciprocated. He did, indeed, have a 'sissy' strea...

Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

LMC Ch. 02: The Camping Trip

by BobbieKayeCutie on Mar 13, 2019
Exhibitionist & Voyeur

Some years ago, an excellent writer of adult fiction, writing under the pseudonym "Little Joe," created several characters inspired by myself and several lovely ladies we both knew. One character was based on me, Bobbie Kaye, and was nicknamed Cutie, or Little Miss Cutie. Little Joe posted a number of these wonderful stories, in which Bobbie Kaye and her fri...

Wet Dream Pt. 03

by sissymissyct on Jan 28, 2020
Fetish

Gayle finished ordering items on line and checked the cam to be sure Georgia was asleep. The wetness in her panties told her what she needed to do. The payback for all those years that bastard cheated on her and how he had no idea what was coming to him, just made her pussy so wet. She was soon in bed enjoying her favorite toy. "I can't believe I slept so l...

Becoming CD Mistress Raven's Slut Ch. 02

by Vodka_Jim on Dec 10, 2018
Transgender & Crossdressers

Author's Note: I took some inspiration for this next chapter from some of the comments, both public and private, that I had to the first chapter. In doing so, I've written about things (e.g. forced cross-dressing) that I've never personally experienced. Most of my writing is based on things that I've experienced and that I think I can relate. So, if I've mis...

Chrysalis of Kirsten Ch. 03

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

What's a Sissy to Do?

by _pdy_ on Apr 14, 2020
Transgender & Crossdressers

The following story is a fictional re-imagining of a situation I found myself in. At this moment, I have no real plans to make it into a series like some of my previous work. It's loosely based on true relationships that I've had with some likeminded people over the years, but it is nonetheless fictional. Anyway, I think that's enough from me, on to the stor...